New route to enantiopure MalphaNP acid, a powerful resolution and chiral 1H NMR anisotropy reagent.
New route to enantiopure MalphaNP acid, a powerful resolution and chiral 1H NMR anisotropy reagent.
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获得对映体纯 MalphaNP 酸的新途径,这是一种强大的分辨率和手性 1H NMR 各向异性试剂。
作者:
Junpei Naito;Hiromi Taji;S. Sekiguchi;M. Watanabe;S. Kuwahara;Masataka Watanabe;N. Harada
MalphaNP acid (+/-)-1, 2-methoxy-2-(1-naphthyl)propionic acid, was enantioresolved by the use of phenylalaninol (S)-(-)-4; a diastereomeric mixture of amides formed from acid (+/-)-1 and amine (S)-(-)-4 was easily separated by fractional recrystallization and/or HPLC on silica gel, yielding amides (R;S)-(-)-5a and (S;S)-(+)-5b. Their absolute configurations were determined by X-ray crystallography by reference to the S configuration of the phenylalaninol moiety. Amide (R;S)-(-)-5a was converted to oxazoline (R;S)-(+)-8a, from which enantiopure MalphaNP acid (R)-(-)-1 was recovered. In a similar way, enantiopure MalphaNP acid (S)-(+)-1 was obtained from amide (S;S)-(+)-5b. These reactions provide a new route for the large-scale preparation of enantiopure MalphaNP acid, a powerful chiral reagent for the enantioresolution of alcohols and simultaneous determination of their absolute configurations by (1)H NMR anisotropy.
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DOI:
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发表时间:
2004
期刊:
Chirality, 16,569-585(2004). 16
影响因子:
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作者:
Yusuke Kasai
通讯作者:
Yusuke Kasai
DOI:
--
发表时间:
2004
期刊:
Chirality 16
影响因子:
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作者:
Yusuke Kasai;kazuaki Akasaka;Gabriel E. Job;Junpei Naito.;Yusuke Kasai.;Kazuaki Akasaka.;Junpei Naito;Yusuke Kasai
通讯作者:
Yusuke Kasai
DOI:
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发表时间:
2002
期刊:
Chirality. 14
影响因子:
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作者:
Yusuke Kasai;kazuaki Akasaka;Gabriel E. Job;Junpei Naito.;Yusuke Kasai.;Kazuaki Akasaka.;Junpei Naito;Yusuke Kasai;Krisztina G-Forras;Kazuaki Akasaka;Masashi Kosaka;Yusuke Kasai;Masashi Kosaka;Shunji Ito;Yusuke Kasai.;Masashi Kosaka.;Shunji Ito.;Hiromi Taji
通讯作者:
Hiromi Taji
DOI:
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发表时间:
2002
期刊:
Organic Letters. 4
影响因子:
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作者:
Yusuke Kasai;kazuaki Akasaka;Gabriel E. Job;Junpei Naito.;Yusuke Kasai.;Kazuaki Akasaka.;Junpei Naito;Yusuke Kasai;Krisztina G-Forras;Kazuaki Akasaka;Masashi Kosaka;Yusuke Kasai;Masashi Kosaka;Shunji Ito;Yusuke Kasai.;Masashi Kosaka.;Shunji Ito.;Hiromi Taji;Masashi Kosaka;Takuma Fujita;Kazuhiro Yoshida;Shinji Ito;Hiromi Taji
通讯作者:
Hiromi Taji
DOI:
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发表时间:
2003
期刊:
Chirality 15(3)
影响因子:
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作者:
Kato H;Takita J;Miyazaki T;Nakajima M;Fukai Y;Masuda N;Fukuchi M;Manda R;Ojima H;Tsukada K;Kuwano H;Oriuchi N;Endo. K.;Yamada K;SATOSHI ISHIDA;S.Arita
通讯作者:
S.Arita